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【结 构 式】 
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【分子编号】39092 【品名】1-[([[(ethoxycarbonyl)amino]oxy]carbonyl)oxy]ethane 【CA登记号】 |
【 分 子 式 】C6H11NO5 【 分 子 量 】177.15708 【元素组成】C 40.68% H 6.26% N 7.91% O 45.16% |
合成路线1
该中间体在本合成路线中的序号：(XVII)5) The condensation of 1-chloro-3-bromopropane (XII) with dibutyl phosphonate (XIII) affords dibutyl 3-chloropropylphosphonate (XIV), which by reaction with ethyl N-benzyloxycarbamate (A) is converted into dibutyl 3-(N-benzyloxy-N-ethoxycarbonylamino)propylphosphonate (XV). Finally, this compound is hydrolyzed with HCl in acetic acid to obtain compound (I). 6) The reaction of (XII) with diethyl phosphonate (III) yields diethyl 3-chloropropylphosphonate (XVI), which by condensation with ethyl N-ethoxycarbonyl-oxycarbamate (XVII) is converted into diethyl 3-(N-ethoxycarbonyloxy-N-ethoxycarbonylamino)propylphosphonate (XVIII). Finally, this compound is hydrolyzed with HCl in acetic acid to obtain compound (I).
| 【1】 Kuroda, Y.; et al.; US 4143135 . |
| 【2】 Prous, J.R.; Castaner, J.; FR-31564. Drugs Fut 1980, 5, 5, 239. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 39093 | ethyl benzyloxycarbamate | C10H13NO3 | 详情 | 详情 | |
| (I) | 39088 | 3-(hydroxyamino)propylphosphonic acid | C3H10NO4P | 详情 | 详情 | |
| (III) | 12714 | diethyl phosphonate; diethyl phosphite | 762-04-9 | C4H11O3P | 详情 | 详情 |
| (XII) | 10358 | 1-Bromo-3-chloropropane | 109-70-6 | C3H6BrCl | 详情 | 详情 |
| (XIII) | 39089 | diethyl 3-chloropropylphosphonate | C7H16ClO3P | 详情 | 详情 | |
| (XIV) | 39091 | dibutyl 3-chloropropylphosphonate | C11H24ClO3P | 详情 | 详情 | |
| (XV) | 39095 | dibutyl 3-[(benzyloxy)(ethoxycarbonyl)amino]propylphosphonate | C21H36NO6P | 详情 | 详情 | |
| (XVI) | 39090 | dibutyl phosphonate | 1809-19-4 | C8H19O3P | 详情 | 详情 |
| (XVII) | 39092 | 1-[([[(ethoxycarbonyl)amino]oxy]carbonyl)oxy]ethane | C6H11NO5 | 详情 | 详情 | |
| (XVIII) | 39094 | 4-ethoxy-8-(ethoxycarbonyl)-4,10-dioxo-3,9,11-trioxa-8-aza-4lambda(5)-phosphatridecane | C13H26NO8P | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XVI)The condensation of hydroxylamine with two equivalents of ethyl chloroformate (XV) afforded (XVI). The potassium salt of (XVI) was then alkylated with bromopropyl phosphonate (V) to yield (XVII), which was subsequently hydrolyzed to the intermediate (VIII) using HCl in HOAc.
| 【1】 Takeno, H.; Hemmi, K.; Hashimoto, M.; Kamiya, T. (Fujisawa Pharmaceutical Co., Ltd.); Hydroxyaminohydrocarbonphosphonic acids. DE 2733658; US 4182758; US 4206156 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 39080 | diethyl 3-bromopropylphosphonate | C7H16BrO3P | 详情 | 详情 | |
| (VIII) | 39088 | 3-(hydroxyamino)propylphosphonic acid | C3H10NO4P | 详情 | 详情 | |
| (XV) | 11229 | 1-[(Chlorocarbonyl)oxy]ethane;ethyl carbonochloridate; Carbonchloridic acid ethyl ester;Ethyl chloroformate;Ethyl chlorocarbonate | 541-41-3 | C3H5ClO2 | 详情 | 详情 |
| (XVI) | 39092 | 1-[([[(ethoxycarbonyl)amino]oxy]carbonyl)oxy]ethane | C6H11NO5 | 详情 | 详情 | |
| (XVII) | 39094 | 4-ethoxy-8-(ethoxycarbonyl)-4,10-dioxo-3,9,11-trioxa-8-aza-4lambda(5)-phosphatridecane | C13H26NO8P | 详情 | 详情 |